Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade

Herein, we report an unprecedented Rh(III)-catalyzed C–H activation/annulation cascade of readily available enaminones with iodonium ylides towards the convenient synthesis of isocoumarins. This coupling system proceeds in useful chemical yields (up to 93%) via a cascade C–H activation, Rh-carbenoid...

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Autores principales: Gao, Qian-Ci, Li, Yi-Fei, Xuan, Jun, Hu, Xiao-Qiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9907013/
https://www.ncbi.nlm.nih.gov/pubmed/36761471
http://dx.doi.org/10.3762/bjoc.19.10
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author Gao, Qian-Ci
Li, Yi-Fei
Xuan, Jun
Hu, Xiao-Qiang
author_facet Gao, Qian-Ci
Li, Yi-Fei
Xuan, Jun
Hu, Xiao-Qiang
author_sort Gao, Qian-Ci
collection PubMed
description Herein, we report an unprecedented Rh(III)-catalyzed C–H activation/annulation cascade of readily available enaminones with iodonium ylides towards the convenient synthesis of isocoumarins. This coupling system proceeds in useful chemical yields (up to 93%) via a cascade C–H activation, Rh-carbenoid migratory insertion and acid-promoted intramolecular annulation. The success of gram-scale reaction and diverse functionalization of isocoumarins demonstrated the synthetic utility of this protocol.
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spelling pubmed-99070132023-02-08 Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade Gao, Qian-Ci Li, Yi-Fei Xuan, Jun Hu, Xiao-Qiang Beilstein J Org Chem Letter Herein, we report an unprecedented Rh(III)-catalyzed C–H activation/annulation cascade of readily available enaminones with iodonium ylides towards the convenient synthesis of isocoumarins. This coupling system proceeds in useful chemical yields (up to 93%) via a cascade C–H activation, Rh-carbenoid migratory insertion and acid-promoted intramolecular annulation. The success of gram-scale reaction and diverse functionalization of isocoumarins demonstrated the synthetic utility of this protocol. Beilstein-Institut 2023-01-30 /pmc/articles/PMC9907013/ /pubmed/36761471 http://dx.doi.org/10.3762/bjoc.19.10 Text en Copyright © 2023, Gao et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Letter
Gao, Qian-Ci
Li, Yi-Fei
Xuan, Jun
Hu, Xiao-Qiang
Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade
title Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade
title_full Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade
title_fullStr Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade
title_full_unstemmed Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade
title_short Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade
title_sort practical synthesis of isocoumarins via rh(iii)-catalyzed c–h activation/annulation cascade
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9907013/
https://www.ncbi.nlm.nih.gov/pubmed/36761471
http://dx.doi.org/10.3762/bjoc.19.10
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